Siena is often overshadowed by its Tuscan cousin, Florence. But this city has some real gems to discover, making it a worthwhile stop on a Tuscan road-trip and even to stay for a week or two, if you please. The thing many find when they stop off in Siena is that its magic captivates you to linger here longer. To enjoy the fine details; craftsmanship in the stalls and art; the people and their traditions; the Gothic architecture and many galleries and museums. Siena surely doesn’t disappoint with its rich atmosphere and offerings, especially during the season of its traditional Palio horse race held in its medieval square.
If you find yourself drawn to Siena for a week’s holiday, we’ve pulled together this fantastic itinerary to keep you busy for seven days:
Day One: Arrival
Your holiday will begin as most do: at the airport. Siena does have its own airport, but this is used for only private flights so your closest option will be Florence Peretola which is around 84km from Siena. Alternatives include Pisa Galileo Galilei and Rome Fiumicino. Of course, we can advise you on your best choice.
Travel can be arranged by train, bus or private hire to your accommodation. We would recommend hiring a car so you can explore Tuscany. Once at your villa, drop off your belongings and settle into your home-away-from-home for the week. With breath-taking views across Tuscan hills, a patio with a pool and multiple rooms to explore, you are bound to spend most of the morning here.
Spend your first afternoon here taking in the sights and sounds of Siena’s Piazza del Campo. In one of the many bars lining the centre, be sure to have a delicious aperitif; the locals prefer the Bar II Palio.
Day Two: Explore Siena’s City Attractions
While most would start back at the Campo for a coffee, we recommend you begin somewhere else. The Piazza Salimbeni is one of the squares based in the centre of Siena. It houses the offices for one of the first banking houses within Europe known as Banca Monte dei Paschi which was founded in 1472. Today, it is the world’s oldest surviving bank. What’s more, churches and palaces of neo-gothic design surround the square. Here, the Spannocchi stands, Siena’s first Renaissance palazzo erected in 1473.
After a morning of marvelling, walk south to the Banchi di Sopra which is lined with shops, dipping into them as you please. But be sure not to waste time as there is plenty more to see on this track including the 13th-century Palazzo Tolomei. Close by, the site of Roman baths. Stop here and explore, or head on to the Piazza San Giovanni to behind the cathedral. To the right, you can follow the Via dei Fusari for a breath-taking view of the cathedral.
Explore the intricate exterior of the Duomo, the second largest cathedral in Tuscany. An Opa Si Pass can be bought for around £10 at the Museo dell’Opera to gain entry to the Duomo, the baptistery, crypt and museum. Inside, artworks such as Michelangelo sculptures stand, along with other collections including works from Duccio – Siena’s greatest painter.
Wow– what a packed morning! Stop off for a spot of late lunch, trying some Tuscan classics to replenish after a busy couple of hours.
Head back to your villa to enjoy an afternoon soaking up the sun and recharge your batteries for day three.
Day Three: Shopping Spree
It’s all about taking it easy today. Mull around Siena’s beautiful streets, taking the time to find keepsakes of your holiday (as well as the much-demanded presents for family and friends left back home). Head back to the familiar Via Banchi di Sopra as your starting point, after a well-needed coffee to begin the morning. This area is regarded as the main shopping street of Siena, and it is here that you will find many of the boutiques for clothes, bags and shoes. Heading away from Banchi di Sopra through via di Citta you will find a collection of shops to source your Italian souvenirs and local handicrafts for presents. Most notable keepsakes include the bandiera (or incontrada flags) that represent families. You can pick a favourite symbol and colour and take these back as gifts.
Siena is also known for its sweet treats and pastries including Panforte and Ricciarelli, so be sure to try them. Manganelli 1879 on Via di Citta is considered one of Italy’s greatest delicatessens so don’t miss it.
Don’t forget to also pop into Sonia’ shop behind the Duomo at Via Fusari. The owner creates handmade ceramics right on the premise. If you can find room in your suitcase, you must not leave without something.
If the shopping bug has caught you, there is a small mall located in the train station, accessible from Via Vittorio Emanuele II. Alternatively, enjoy the sunshine by meandering through one of the many outdoor markets. You can purchase a collection of products here, from groceries, bags, clothes, jewellery and home utensils. You will find this market on Wednesdays from 7 am to 1 pm down at the Piazza Gramsci around the Fortezza and La Lizza park. Good finds can be found here at low prices. It is advised to be cautious of your belongings when packed.
Other notable markets include the farmer’s market on Friday mornings (located at the same place as the Wednesday market). Although, the market is small, fresh and quality produce can be bought to take back to the villa for a magnificent feast! If you feel you may miss this market, high-quality local products can be bought from the Consorzio Agrario at Via Giuseppe Pianigiani.
And much like other places in Italy, an antiques fair is held on the third Sunday of the month at the Piazza del Mercato (close to the Piazza del Campo).
In Siena, sales run in January and July, with prices cut to almost 50 to 75% of the general RRP.
The saying “shop ‘till you drop” has never been so true when you discover Siena’s offerings. Head back to the villa to put your feet up, ideally with a treat or two to nibble on!
Day Four: Museums and Galleries
There’s no getting away from the museums and galleries when you visit Italy – and why would you want to anyway? Inside Siena’s town hall, the Museo Civico waits for your visit. Rooms patterned with frescoes and vaults, a tour around this museum is something else. Paintings showcased here include the Simone Martini’s Maestà (1315) and The Allegory of Good and Bad Government (1338).
Inside the Pinacoteca Nazionale gallery is an extensive collection of Sienese paintings starting from the 12th-century. Art-lovers and history-buffs alike will find this gallery delightful. Once complete, head to the Santa Maria della Scala. The history of this building was that it was once Siena’s main hospital for over 800 years. In 1995, the building was repurposed to become another gallery hosting a wonderful array of art.
Day Five: Road trip Around the Local Area
A rented car is vital for today. Head southeast from Siena through hills and cypress alleys for about an hour to reach Pienza, a much-loved UNESCO site. Here Renaissance buildings meet a sleepy town atmosphere with plenty to offer in terms of food. Next, make your way only 15km east to the town of Montepulciano for more food, coupled with fantastic wine. The vineyards of Val d’Orcia make for a beautiful tour of one of Tuscany’s most treasured tourist attractions. Be sure to try the Chianina beef accompanied with some fresh olive oil and a little glass of wine.
Day Six: Relax and Pack
Take today to relax in your luxury holiday villa. Tuscany has plenty more to offer, however, so if you have more energy, head in the car to explore. Alternatively, if the week has felt non-stop, take today as a well-deserved break. Pop your feet up by the pool or take a sun-kissed dip in the water. Go for a leisurely walk in the countryside around your villa, or indulge in a great book. However, if you like to relax, make sure to take today to unwind.
When all the relaxing has come to a natural end, open up the suitcase to pack ready for tomorrow.
Day Seven: Home Time
We’ll be sad to see you leave the villa today. We’re sure you’ll be sad to leave, too! Say farewell to the views and the villa, and make your way to the airport.
For more information on Siena or for guidance, head to the tourist office in the Campo (No. 57). Here they can help you organise fantastic guides and walks. Alternatively, do not hesitate to get in touch with us and we can help you plan a Tuscan holiday you will never forget!
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